Acetic Anhydride → HCID 86660589, compound

HRID 718728Notes

Reaction equation

HRID 718728 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:42])[N:12]([C:19]1([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:24][CH2:23][C:22](=[O:25])[NH:21][C:20]1=[O:26])[C:13]2=[O:18]>N1C=CC=CC=1>[C:1]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11](=[O:42])[N:12]([C:19]1([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:41])[O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:24][CH2:23][C:22](=[O:25])[NH:21][C:20]1=[O:26])[C:13]2=[O:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86660586HCID 86660586, compound

Product 1

HCID 86660589HCID 86660589, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of acetic anhydride (0.098 mL, 1.04 mmol) in pyridine (1 mL) was added 6 (0.05 g, 0.104 mmol) and the mixture was stirred at 70° C. After 12 h, the mixture was quenched with 1% aqueous HCl and extracted with DCM. The organic layer was dried over MgSO4 and concentrated. Preparatory thin layer chromatography (1:1 EtOAc:hexanes) afforded 15 (0.02 g, 37%) as an impure product that was used in the subsequent reaction. Rf=0.16 (1:1 EtOAc:hexanes).

Workup

  1. customthe mixture was quenched with 1% aqueous HCl
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a118377800a43468d37de2f46919863
Source dataset
uspto-grants-2015_11
Patent number
US09193989B2

Reaction notes

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